Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes

Martinez-Cuezva, Alberto; Lopez-Leonardo, Carmen; Alajarín, Mateo; Berná Cánovas, José

Publication:
Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes

dc.contributor.author	Martinez-Cuezva, Alberto
dc.contributor.author	Lopez-Leonardo, Carmen
dc.contributor.author	Alajarín, Mateo
dc.contributor.author	Berná Cánovas, José
dc.contributor.department	Química Orgánica
dc.date.accessioned	2021-02-03T06:40:18Z
dc.date.available	2021-02-03T06:40:18Z
dc.date.created	2019
dc.date.issued	2019-01-18
dc.description.abstract	β-Lactams are highly valuable compounds due to their antibiotic activity. Among the number of well-established methodologies for building this privileged scaffold, our research group has settled on a novel synthetic approach for their preparation. This Account focuses on our latest progress in the synthesis of these compounds through a novel base-promoted intramolecular cyclization of benzylfumaramide-based rotaxanes. The mechanical bond plays a significant role in the process by activating the cyclization inside the macrocycle void, avoiding the formation of byproducts and fully controlling the diastereoselectivity. Further investigations on this transformation led to the formation of enantioenriched 2-azetidinones. The cyclization of enantiopure interlocked α-methylbenzylfumaramides allows the formation of two new stereogenic centers in the lactamic four-membered ring, one of them a quaternary carbon, keeping the initial configuration of the chiral group of the starting material.	es
dc.format	application/pdf	es
dc.format.extent	10	es
dc.identifier.citation	Synlett 2019, 30, 893–902.
dc.identifier.doi	10.1055/s-0037-1611705
dc.identifier.issn	0936-5214
dc.identifier.issn	1437-2096
dc.identifier.uri	http://hdl.handle.net/10201/102481
dc.language	eng	es
dc.publisher	Thieme	es
dc.relation	(I) Ministerio de Economía, Industria y Competitividad. Programa Estatal de Fomento de la Investigación Científica y Técnica de Excelencia. Proyectos I+D 2017 (Nacional). Nombre del proyecto: Reactividad y Conmutación de Moléculas Mecanizadas. Código: CTQ2017-87231-P. (II) Fundación Séneca (Comunidad Autónoma de la Región de Murcia). Ayudas a la realización de proyectos para el desarrollo de investigación científica y técnica por grupos competitivos 2018 (Regional). Nombre del proyecto: Compuestos Entrelazados para el Ensamblaje de Sistemas Funcionales. Código: 20811/PI/18	es
dc.relation.isreplacedby	https://doi.org/10.1055/s-0037-1611705	es
dc.relation.publisherversion	https://www.thieme-connect.com/products/ejournals/html/10.1055/s-0037-1611705	es
dc.rights	info:eu-repo/semantics/openAccess	es
dc.rights	Atribución-NoComercial-SinDerivadas 3.0 España	*
dc.rights.uri	http://creativecommons.org/licenses/by-nc-nd/3.0/es/	*
dc.subject	mechanical bonding	es
dc.subject	cyclization	es
dc.subject	stereoselectivity	es
dc.subject	beta-lactams	es
dc.subject	macrocycles	es
dc.subject.other	CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica	es
dc.title	Stereocontrol in the Synthesis of β-Lactams Arising from the Interlocked Structure of Benzylfumaramide-Based Hydrogen-Bonded [2]Rotaxanes	es
dc.type	info:eu-repo/semantics/article	es
dspace.entity.type	Publication	es